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A9501

Adenosine 3′,5′-cyclic monophosphate

Name: Adenosine 3&#8242;,5&#8242;-cyclic monophosphate
Brand: SIGMA

≥98.5% (HPLC), powder, PKA activator

Synonym(s):

3′,5′-Cyclic AMP, Adenosine 3′,5′-cyclophosphate, cAMP

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About This Item

Empirical Formula (Hill Notation):

C₁₀H₁₂N₅O₆P

CAS Number:

60-92-4

Molecular Weight:

329.21

NACRES:

NA.77

PubChem Substance ID:

24278245

eCl@ss:

32160414

UNSPSC Code:

41106305

EC Number:

200-492-9

MDL number:

MFCD00005845

Beilstein/REAXYS Number:

52645

Assay:

≥98.5% (HPLC)

Form:

powder

Quality level:

200

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Properties

Product Name

Adenosine 3′,5′-cyclic monophosphate, ≥98.5% (HPLC), powder

Quality Level

200

assay

≥98.5% (HPLC)

form

powder

color

white

mp

260 °C (dec.) (lit.)

solubility

H₂O: 10 mg/mL, clear, colorless (pH of aqueous solution is approx. 3.0. The sodium salt (A6885) is about 20× more soluble.)

storage temp.

−20°C

SMILES string

Nc1ncnc2n(cnc12)[C@@H]3O[C@@H]4COP(O)(=O)O[C@H]4[C@H]3O

InChI

1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1

InChI key

IVOMOUWHDPKRLL-KQYNXXCUSA-N

Gene Information

human ... OPRK1(4986)

Description

Application

Adenosine 3′,5′-cyclic monophosphate has been used:

as cell culture medium supplement in embryonic spinal neurons
as a component of ringer solution for perfusion studies
to induce neuroendocrine differentiation in human lung cancer cell lines

Biochem/physiol Actions

Naturally-occurring activator of cyclic-AMP-dependent protein kinase (PKA). The cAMP/PKA signaling pathway inhibits cell proliferation, induces differentiation and leads to apoptosis.

Naturally-occurring activator of cyclic-AMP-dependent protein kinase (PKA). cAMP is an important second messenger that is linked in many systems to neurotransmitter- or hormone-induced receptor stimulation. The cAMP/PKA signaling pathway has been shown to inhibit cell proliferation, induce differentiation and lead to apoptosis.

Features and Benefits

This compound is a featured product for ADME Tox and Cyclic Nucleotide research. Discover more featured ADME Tox and Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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